“In 2020, with so many good choices like Elizabeth Warren and Bernie Sanders in the race, voters will obviously apply a lot more scrutiny to a candidate's worldview,” said Adam Green, the PCCC co-founder.

He mentioned "Medicare For all," the Green New Deal climate change plan and efforts to allow students to graduate from college debt-free as among the issues on which O’Rourke will face scrutiny.

On Medicare For all, progressives have highlighted what they say are O’Rourke’s conflicting messages.

While serving in Congress, O’Rourke described a single-payer Medicare for all program as the best way to ensure all Americans get the health care they need.

But during his Senate campaign he coined it a different way, saying Texans needed “universal, guaranteed, high-quality health care” while shying away from backing Medicare for all.

Did he wait too long?

O’Rourke was one of the hottest political brands in the country after the midterm elections when he ran a surprisingly close race against Cruz and showed off impressive fundraising skills.

Voters said he was the future of the party, and he instantly drew comparisons to former President Obama.

But O’Rourke’s star has faded a bit since those days.

He faced criticism for appearing unfocused as he took a cross-country road trip and wrote a Medium post about being “stuck” and “in and out of a funk.”

He also took his social media followers along as he visited a dentist, becoming the butt of jokes on Twitter and causing some to openly wonder if he had missed his opportunity.

But there are also those wondering if O’Rourke needed to more decisive about the race late last year in order to preserve the clear momentum he had at the time.

Can he win Iowa?

O’Rourke headed straight to the Hawkeye State after launching his campaign in El Paso.

The move suggests he sees a strong result in Iowa as being a key for his White House path.

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“He’s the great unknown here in Iowa,” said Pat Rynard, who runs the popular political site Iowa Starting Line. “People watched his Senate race from afar, but he didn't make any early trips so Iowans haven’t gotten up close and personal with him yet.”

Steffen Schmidt, a professor of political science at Iowa State University, said there is “a lot of interest” in O’Rourke. “He seems dynamic and charismatic and he'll get a good turnout at events.”

Petkanas said the crowded field will make the Iowa caucuses even more important.

“I think Iowa is going to be crucial for most candidates, but especially those like Beto who need at least a decent showing with the super liberal constituency that frequents those caucuses,” he said.

How much will losing to Cruz hurt O’Rourke?

Winning the White House isn’t easy, and most who do so aren’t rebounding from a political defeat in a congressional race.

Republicans have sought to use O’Rourke’s loss to Cruz as a way of defining him as, well, a loser.

“After losing his Senate bid in Texas, the Liberals’ lovable loser who has been road tripping, live-streaming, and finding himself, decided he wants to lost on a bigger stage,” a statement from the Republican National Committee blared.

Democrats may also use the Cruz loss against O’Rourke.

“If Beto O'Rourke wants to go and run for president, God bless him. He should put his hat in and make his case. But he lost. You don't promote a loser to the top of the party,” Chicago Mayor Rahm Emanuel said late last year during an appearance on MSNBC’s “Morning Joe.”

Is O’Rourke underestimated?

Being compared to Obama isn’t easy and sets a high standard for O’Rourke.

Critics say such comparisons are overblown and unfair to the Texan.

“Apart from maybe his charisma, they’re totally different people,” said one former aide to Obama.

Yet if there is a sense among some that O’Rourke gets more hype than he deserves, there are others who say it would be foolish to underestimate him.